The fate of Obamacare could reside in the hands of one of these 2 people

The fate of the Affordable Care Act is in the hands of the
Supreme Court once again — and whether it lives as is or crumbles
might depend on a justice who believes the heart of the law to be
unconstitutional.

Justice Anthony Kennedy is the traditional swing vote, and his
views on the latest death threat to the law colloquially known as
Obamacare will most likely predict how the court rules.

The fate of the decision could also rest with conservative Chief
Justice John Roberts, who previously sided with the liberals to
uphold the law.

The high court's decision could be handed down as soon as Monday
and is expected to be delivered sometime before the end of the
month.

This latest challenge puts Kennedy in a particularly vexing
position.

Just three years ago, he voted against the government and opined
that the heart of the Affordable Care Act — its individual
mandate requiring individuals to purchase some form of health
insurance or pay a penalty — was unconstitutional. Kennedy read
his dissent from the bench with a palpable display of emotion
after Roberts joined the liberals to save the law.

"It amounts to a vast judicial overreaching," Kennedy said of the
5-4 decision that upheld the mandate's penalty as a tax.

Now Kennedy might be the one to save a key provision of the law.
This challenge, King v. Burwell, has the potential to cripple the
law and throw its future into highly uncertain territory in the
36 states in which the federal government provides subsidies for
low-income people to buy health insurance. And Kennedy and
Roberts are again the justices to watch.

"They're going to be the swing votes," said Jonathan Adler, a
professor at Case Western University School of Law and one of the
lawyers instrumental in forming the challenge.

"And I expect them to vote together, whichever way they vote."

The challengers in King v. Burwell are focusing on four words in
the statute that they say suggest the federal government can't
subsidize health insurance in the 36 states that refused to set
up their own exchanges. Those four words are in Section 1311 of
the law, which establishes insurance exchanges. That section
states that subsidies should be issued to plans purchased
"through an Exchange established by the State under Section 1311"
of the Affordable Care Act.

Chief Justice John
Roberts, left, and Justice Anthony Kennedy before President
Obama's State of the Union speech in 2013.Reuters/Charles Dharapak

Kennedy was the justice targeted by both the challengers and the
Obama administration during oral arguments in March. And each
side saw points in which it thought he was leaning its way. In
one exchange, he seemed to worry about the coercing effects a
decision against the healthcare law would have on states to set
up their own insurance marketplaces.

During another, he said the challengers "may prevail" on the
"plain words of the statute," even though he acknowledged a
"serious constitutional problem if we adopt your argument."

Chris Walker, an assistant professor at the Michael E. Moritz
College of Law who clerked for Kennedy, told Business Insider
that Kennedy could go either way.

"A lot of the questions he was asking were about federalism, and
federalism is something he cares deeply about," Walker said.

On the flip side, near the end of the oral argument, Kennedy
asked Solicitor General Donald Verrilli — who represents the
Obama administration — about how much authority the IRS should
have in interpreting a law passed by Congress,
as Slate's Dahlia Lithwick noted. It was the IRS that
interpreted the law to allow subsidies in states with exchanges
set up by the federal government.

Kennedy questioned whether Congress really meant for the IRS
rather than the states to make a decision with potentially
billions of dollars at stake.

"[I]t seems to me a drastic step for us to say that the
Department of Internal Revenue Service and its director can make
this call one way or the other when there are, what, billions of
dollars of subsidies involved here? Hundreds of millions?"
Kennedy said during the oral arguments.

"So you've got these bookends," Walker told Business Insider. "At
the beginning, he seems very concerned about the federalism
argument. And at the end of the argument, he seems to be
concerned about executive power and congressional interpretation.
So it's difficult to figure out where he stands."

The states and counties
that will be affected by a ruling against the Obama
administration.Washington Center for
Equitable Growth

Roberts is much harder to figure out, and Supreme Court observers
say they're entirely uncertain which way he'll lean. On one hand,
he upheld the law last time. On the other hand, he's viewed as
generally pro-business in his decisions, and multiple businesses
and organizations have issued briefs on the side of the
administration in this case.

Complicating things is the fact that Roberts spoke just two
meaningful times during the oral arguments. That was as often as
the number of times he opened his mouth to crack a joke at one of
the lawyers involved in the case.

Kennedy has been more of a talker. In fact, just three weeks
after the arguments, he appeared before Congress and said
something that some observers viewed as possibly tipping his hand. He said,
in a general sense and without mentioning the Affordable Care
Act, that the judiciary should decide cases without worrying
about external factors like congressional gridlock.

That comment spurred speculation that he might not have any
qualms about dismantling Obamacare even though lawmakers might
not ever come together to fix the law.

But even Adler, one of the legal minds behind the King challenge,
said those comments didn't raise his hopes.